EP1611107B1 - 1,3,4-substituierte pyrazole als 5-ht rezeptor-antagonisten zur behandlung von psychosen und neurologischen störungen - Google Patents
1,3,4-substituierte pyrazole als 5-ht rezeptor-antagonisten zur behandlung von psychosen und neurologischen störungen Download PDFInfo
- Publication number
- EP1611107B1 EP1611107B1 EP04718264A EP04718264A EP1611107B1 EP 1611107 B1 EP1611107 B1 EP 1611107B1 EP 04718264 A EP04718264 A EP 04718264A EP 04718264 A EP04718264 A EP 04718264A EP 1611107 B1 EP1611107 B1 EP 1611107B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- pyrazol
- ylmethyl
- furan
- denotes
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000011282 treatment Methods 0.000 title claims description 22
- 208000028017 Psychotic disease Diseases 0.000 title claims description 4
- 208000012902 Nervous system disease Diseases 0.000 title claims description 3
- 208000025966 Neurological disease Diseases 0.000 title claims description 3
- 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 title description 2
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 239000012453 solvate Substances 0.000 claims abstract description 39
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims abstract description 5
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims abstract description 5
- -1 ethyl- Chemical group 0.000 claims description 70
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- UYQFQCKYZLGKMQ-UHFFFAOYSA-N 1-[[3-(furan-2-yl)-1-(4-thiophen-3-ylphenyl)pyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CN(C=2C=CC(=CC=2)C2=CSC=C2)N=C1C1=CC=CO1 UYQFQCKYZLGKMQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- RRWCULUAWKAUNJ-UHFFFAOYSA-N 1-[[3-(2-fluorophenyl)-1-(4-phenylphenyl)pyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CN(C=2C=CC(=CC=2)C=2C=CC=CC=2)N=C1C1=CC=CC=C1F RRWCULUAWKAUNJ-UHFFFAOYSA-N 0.000 claims description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- LOAMHOUVUJPVJE-UHFFFAOYSA-N 1-(1,3-diphenylpyrazol-4-yl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 LOAMHOUVUJPVJE-UHFFFAOYSA-N 0.000 claims description 3
- GCVCSJPTLSTSEZ-UHFFFAOYSA-N 1-[(1,3-diphenylpyrazol-4-yl)methyl]-4-ethylpiperazine Chemical compound C1CN(CC)CCN1CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 GCVCSJPTLSTSEZ-UHFFFAOYSA-N 0.000 claims description 3
- VVZRZRXDDDUKOX-UHFFFAOYSA-N 1-[(1,3-diphenylpyrazol-4-yl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 VVZRZRXDDDUKOX-UHFFFAOYSA-N 0.000 claims description 3
- ZMMRIONHZXULFC-UHFFFAOYSA-N 1-[3-(2-fluorophenyl)-1-phenylpyrazol-4-yl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1F ZMMRIONHZXULFC-UHFFFAOYSA-N 0.000 claims description 3
- BUPQBGPSLXNELO-UHFFFAOYSA-N 1-[[1-(4-bromophenyl)-3-(furan-2-yl)pyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CN(C=2C=CC(Br)=CC=2)N=C1C1=CC=CO1 BUPQBGPSLXNELO-UHFFFAOYSA-N 0.000 claims description 3
- OQLLFPVYVABJPG-UHFFFAOYSA-N 1-[[1-(4-butylphenyl)-3-(furan-2-yl)pyrazol-4-yl]methyl]pyrrolidin-3-ol Chemical compound C1=CC(CCCC)=CC=C1N1N=C(C=2OC=CC=2)C(CN2CC(O)CC2)=C1 OQLLFPVYVABJPG-UHFFFAOYSA-N 0.000 claims description 3
- YKZURXNDHGYIOB-UHFFFAOYSA-N 1-[[1-[4-(1,3-benzodioxol-5-yl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CN(C=2C=CC(=CC=2)C=2C=C3OCOC3=CC=2)N=C1C1=CC=CO1 YKZURXNDHGYIOB-UHFFFAOYSA-N 0.000 claims description 3
- ZXJKSGUUIPLQCB-UHFFFAOYSA-N 1-[[1-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1CC1=CN(C=2C=CC(=CC=2)C=2C=C3OCCOC3=CC=2)N=C1C1=CC=CO1 ZXJKSGUUIPLQCB-UHFFFAOYSA-N 0.000 claims description 3
- XUYBYXWSTRQCQL-UHFFFAOYSA-N 1-[[1-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]piperazine Chemical compound C=1N(C=2C=CC(=CC=2)C=2C=C3OCCOC3=CC=2)N=C(C=2OC=CC=2)C=1CN1CCNCC1 XUYBYXWSTRQCQL-UHFFFAOYSA-N 0.000 claims description 3
- ZYNOAGVPKKCZSF-UHFFFAOYSA-N 1-[[1-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CN(C=2C=CC(=CC=2)C=2C=C3OCCOC3=CC=2)N=C1C1=CC=CO1 ZYNOAGVPKKCZSF-UHFFFAOYSA-N 0.000 claims description 3
- NBZRAZBCLSBXEG-UHFFFAOYSA-N 1-[[1-[4-(3-fluorophenyl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1CC1=CN(C=2C=CC(=CC=2)C=2C=C(F)C=CC=2)N=C1C1=CC=CO1 NBZRAZBCLSBXEG-UHFFFAOYSA-N 0.000 claims description 3
- FADWGDXEBLEIEC-UHFFFAOYSA-N 1-[[1-[4-(3-fluorophenyl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CN(C=2C=CC(=CC=2)C=2C=C(F)C=CC=2)N=C1C1=CC=CO1 FADWGDXEBLEIEC-UHFFFAOYSA-N 0.000 claims description 3
- RFMMIVBYZBIXKU-UHFFFAOYSA-N 1-[[1-[4-(4-fluorophenyl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1CC1=CN(C=2C=CC(=CC=2)C=2C=CC(F)=CC=2)N=C1C1=CC=CO1 RFMMIVBYZBIXKU-UHFFFAOYSA-N 0.000 claims description 3
- MAQCZOUFJUZUQJ-UHFFFAOYSA-N 1-[[1-[4-(4-fluorophenyl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]piperazine Chemical compound C1=CC(F)=CC=C1C1=CC=C(N2N=C(C(CN3CCNCC3)=C2)C=2OC=CC=2)C=C1 MAQCZOUFJUZUQJ-UHFFFAOYSA-N 0.000 claims description 3
- VDOYKSHUYHYAGH-UHFFFAOYSA-N 1-[[3-(2-fluorophenyl)-1-phenylpyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1F VDOYKSHUYHYAGH-UHFFFAOYSA-N 0.000 claims description 3
- AKUNVPXOSPUULI-UHFFFAOYSA-N 1-[[3-(2-fluorophenyl)-1-phenylpyrazol-4-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1F AKUNVPXOSPUULI-UHFFFAOYSA-N 0.000 claims description 3
- YNTCHOAGPQZFHN-UHFFFAOYSA-N 1-[[3-(furan-2-yl)-1-[4-(4-methoxyphenyl)phenyl]pyrazol-4-yl]methyl]piperazine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2N=C(C(CN3CCNCC3)=C2)C=2OC=CC=2)C=C1 YNTCHOAGPQZFHN-UHFFFAOYSA-N 0.000 claims description 3
- YZDFWBCXFJYZHV-UHFFFAOYSA-N 1-[[3-(furan-2-yl)-1-[4-(4-methoxyphenyl)phenyl]pyrazol-4-yl]methyl]pyrrolidin-3-ol Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2N=C(C(CN3CC(O)CC3)=C2)C=2OC=CC=2)C=C1 YZDFWBCXFJYZHV-UHFFFAOYSA-N 0.000 claims description 3
- VYPZFNXDGKXNEY-UHFFFAOYSA-N 1-cyclopentyl-4-[[1-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]piperazine Chemical compound C=1N(C=2C=CC(=CC=2)C=2C=C3OCCOC3=CC=2)N=C(C=2OC=CC=2)C=1CN(CC1)CCN1C1CCCC1 VYPZFNXDGKXNEY-UHFFFAOYSA-N 0.000 claims description 3
- XULYYONTXLEIKQ-UHFFFAOYSA-N 1-ethyl-4-[[3-(2-fluorophenyl)-1-phenylpyrazol-4-yl]methyl]piperazine Chemical compound C1CN(CC)CCN1CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1F XULYYONTXLEIKQ-UHFFFAOYSA-N 0.000 claims description 3
- IVVURJVFESZKFU-UHFFFAOYSA-N 2-[[1-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methylamino]ethanol Chemical compound OCCNCC1=CN(C=2C=CC(=CC=2)C=2C=C3OCCOC3=CC=2)N=C1C1=CC=CO1 IVVURJVFESZKFU-UHFFFAOYSA-N 0.000 claims description 3
- DJVNVCBXPLZFKD-UHFFFAOYSA-N 2-[[1-[4-(3-fluorophenyl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methylamino]ethanol Chemical compound OCCNCC1=CN(C=2C=CC(=CC=2)C=2C=C(F)C=CC=2)N=C1C1=CC=CO1 DJVNVCBXPLZFKD-UHFFFAOYSA-N 0.000 claims description 3
- OMNLGOWLXZBVSB-UHFFFAOYSA-N 2-[[3-(furan-2-yl)-1-[4-(4-methoxyphenyl)phenyl]pyrazol-4-yl]methylamino]ethanol Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2N=C(C(CNCCO)=C2)C=2OC=CC=2)C=C1 OMNLGOWLXZBVSB-UHFFFAOYSA-N 0.000 claims description 3
- XQYRGMQMMUUKQK-UHFFFAOYSA-N 4-[[1-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]morpholine Chemical compound C=1N(C=2C=CC(=CC=2)C=2C=C3OCCOC3=CC=2)N=C(C=2OC=CC=2)C=1CN1CCOCC1 XQYRGMQMMUUKQK-UHFFFAOYSA-N 0.000 claims description 3
- WKRUYGDKRQINGO-UHFFFAOYSA-N 4-[[1-[4-(4-fluorophenyl)phenyl]-3-(furan-2-yl)pyrazol-4-yl]methyl]morpholine Chemical compound C1=CC(F)=CC=C1C1=CC=C(N2N=C(C(CN3CCOCC3)=C2)C=2OC=CC=2)C=C1 WKRUYGDKRQINGO-UHFFFAOYSA-N 0.000 claims description 3
- JHTPHZUEDVRHDD-UHFFFAOYSA-N 4-[[3-(2-fluorophenyl)-1-(4-phenylphenyl)pyrazol-4-yl]methyl]morpholine Chemical compound FC1=CC=CC=C1C1=NN(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1CN1CCOCC1 JHTPHZUEDVRHDD-UHFFFAOYSA-N 0.000 claims description 3
- NRDYWJMWBGNNIQ-UHFFFAOYSA-N 4-[[3-(furan-2-yl)-1-[4-(4-methoxyphenyl)phenyl]pyrazol-4-yl]methyl]morpholine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2N=C(C(CN3CCOCC3)=C2)C=2OC=CC=2)C=C1 NRDYWJMWBGNNIQ-UHFFFAOYSA-N 0.000 claims description 3
- DLQXGJRPZSYHRC-UHFFFAOYSA-N 4-[[3-(furan-2-yl)-1-phenylpyrazol-4-yl]methyl]morpholine Chemical compound C=1N(C=2C=CC=CC=2)N=C(C=2OC=CC=2)C=1CN1CCOCC1 DLQXGJRPZSYHRC-UHFFFAOYSA-N 0.000 claims description 3
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
- 208000032841 Bulimia Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
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- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- KURYHGYHKKLGFP-UHFFFAOYSA-N n-[(1,3-diphenylpyrazol-4-yl)methyl]-n,1-dimethylpyrrolidin-3-amine Chemical compound C1CN(C)CC1N(C)CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 KURYHGYHKKLGFP-UHFFFAOYSA-N 0.000 claims description 3
- RFQWCACKRVKRIM-UHFFFAOYSA-N n-[(1,3-diphenylpyrazol-4-yl)methyl]-n-methylethanamine Chemical compound CCN(C)CC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 RFQWCACKRVKRIM-UHFFFAOYSA-N 0.000 claims description 3
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Definitions
- the compounds of the formula I according to the invention are suitable as ligands of 5HT receptors, so that the compounds according to the invention, and their salts and solvates, enantiomers and racemates, in particular their physiologically acceptable salts and solvates, are suitable for the treatment and prophylaxis of diseases, which can be influenced by the binding of the compounds of the formula I to 5 HT receptors.
- R 5 is preferably Het. Further preferred meanings of R 1 , R 2 , R 5 and Q are shown in the examples.
- A is alkenyl, it is preferably allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, furthermore preferred is 4-pentenyl, iso-pentenyl or 5-hexenyl.
- Ar is preferably an unsubstituted or substituted by Hal, OH, CN, NO 2 , NH 2 , NHCOCH 3 , COOCH 3 CONH 2 or CF 3 phenyl.
- Ar is substituted in the 4- or 3-position.
- the invention also relates to the compounds of the formula I and their physiologically acceptable salts and solvates as glycine transporter inhibitors.
- 500 mg of an active compound of the formula I are mixed with 99.5 g of Vaseline under aseptic conditions.
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Psychology (AREA)
- Reproductive Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Addiction (AREA)
- Pulmonology (AREA)
- Toxicology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Nutrition Science (AREA)
- Child & Adolescent Psychology (AREA)
- Rheumatology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Urology & Nephrology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2003115573 DE10315573A1 (de) | 2003-04-05 | 2003-04-05 | Substituierte Pyrazole |
| PCT/EP2004/002354 WO2004089910A1 (de) | 2003-04-05 | 2004-03-08 | 1,3,4-substituierte pyrazole als 5-ht rezeptor-antagonisten zur behandlung von psychosen und neurologischen störungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1611107A1 EP1611107A1 (de) | 2006-01-04 |
| EP1611107B1 true EP1611107B1 (de) | 2010-08-18 |
Family
ID=32981074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP04718264A Expired - Lifetime EP1611107B1 (de) | 2003-04-05 | 2004-03-08 | 1,3,4-substituierte pyrazole als 5-ht rezeptor-antagonisten zur behandlung von psychosen und neurologischen störungen |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7566709B2 (zh) |
| EP (1) | EP1611107B1 (zh) |
| JP (1) | JP4740116B2 (zh) |
| KR (1) | KR20050119194A (zh) |
| CN (1) | CN1768043A (zh) |
| AR (1) | AR043838A1 (zh) |
| AT (1) | ATE478052T1 (zh) |
| AU (1) | AU2004228121B2 (zh) |
| BR (1) | BRPI0409002A (zh) |
| CA (1) | CA2521202A1 (zh) |
| DE (2) | DE10315573A1 (zh) |
| ES (1) | ES2349922T3 (zh) |
| MX (1) | MXPA05010646A (zh) |
| RU (1) | RU2005133990A (zh) |
| WO (1) | WO2004089910A1 (zh) |
| ZA (1) | ZA200508951B (zh) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10315569A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazolverbindungen |
| DE10315571A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| DE10315572A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| WO2006089076A2 (en) * | 2005-02-18 | 2006-08-24 | Neurogen Corporation | Thiazole amides, imidazole amides and related analogues |
| CN101248049B (zh) * | 2005-06-27 | 2013-08-28 | 埃克塞利希斯专利有限责任公司 | 咪唑类lxr调节剂 |
| AU2006261841B8 (en) | 2005-06-27 | 2012-12-06 | Exelixis Patent Company Llc | Pyrazole based LXR modulators |
| EP1919895A2 (en) | 2005-08-02 | 2008-05-14 | Lexicon Pharmaceuticals, Inc. | 2-aminoaryl pyridines as protein kinases inhibitors |
| JP2008169191A (ja) * | 2006-02-20 | 2008-07-24 | Eisai R & D Management Co Ltd | 運動ニューロン疾患治療剤 |
| CN101679297B (zh) | 2006-12-08 | 2012-01-11 | 埃克塞利希斯股份有限公司 | Lxr和fxr调节剂 |
| US8524909B2 (en) * | 2010-02-02 | 2013-09-03 | Hoffmann-La Roche Inc. | Tetrahydro-pyran derivatives |
| TW201321367A (zh) * | 2011-10-25 | 2013-06-01 | Du Pont | 經１，３－二芳基取代之雜環殺蟲劑 |
| WO2013173218A1 (en) | 2012-05-16 | 2013-11-21 | E. I. Du Pont De Nemours And Company | 1,3-diaryl-substituted heterocyclic pesticides |
| GB201312800D0 (en) | 2013-07-17 | 2013-08-28 | Heptares Therapeutics Ltd | mGlu5 modulators |
| WO2015022293A2 (en) * | 2013-08-12 | 2015-02-19 | Basf Se | 1,3-(het)aryl-substituted pyrazole compounds |
| TW201601632A (zh) | 2013-11-20 | 2016-01-16 | 杜邦股份有限公司 | １－芳基－３－烷基吡唑殺蟲劑 |
| MA54133B1 (fr) | 2018-03-08 | 2022-01-31 | Incyte Corp | Composés d'aminopyrazine diol utilisés comme inhibiteurs de pi3k-y |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146721A (en) | 1969-09-12 | 1979-03-27 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pyrazol-4-acetic acid compounds |
| CH518155A (de) * | 1970-08-18 | 1972-01-31 | Schaerer Willy | Verfahren zur Erleichterung des Schleifens schraubenlinienförmiger Nuten, bei einer Serie von unter sich gleichen Werkstücken mit je mindestens einer schraubenlinienförmig eingefrästen Nut und Simuliergerät zur Durchführung des Verfahrens |
| BE793955A (fr) | 1972-01-15 | 1973-07-12 | Merck Patent Gmbh | Arylpiperazines et leur procede de preparation |
| DE2906252A1 (de) | 1979-02-19 | 1980-08-28 | Merck Patent Gmbh | Pyrazolderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| US4631343A (en) | 1983-11-07 | 1986-12-23 | Eli Lilly And Company | Cyanopyrazole intermediates |
| KR100442561B1 (ko) | 1995-04-20 | 2004-10-14 | 지.디. 썰 엘엘씨 | ５산화２질소신타아제의억제제로유용한환상아미디노제 |
| EP0971588B1 (en) | 1997-01-21 | 2004-03-17 | Smithkline Beecham Corporation | Novel cannabinoid receptor modulators |
| US6150393A (en) | 1998-12-18 | 2000-11-21 | Arena Pharmaceuticals, Inc. | Small molecule modulators of non-endogenous, constitutively activated human serotonin receptors |
| US20010044445A1 (en) | 1999-04-08 | 2001-11-22 | Bamaung Nwe Y. | Azole inhibitors of cytokine production |
| US6632815B2 (en) | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| AU1445001A (en) | 1999-10-29 | 2001-05-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Process of making substituted pyrazoles |
| US6407238B1 (en) | 1999-10-29 | 2002-06-18 | Boehringer Ingelheim Pharmaceuticals, Inc. | Process of making substituted pyrazoles |
| DE60017446T2 (de) | 1999-11-05 | 2006-03-02 | Smithkline Beecham P.L.C., Brentford | Isochinolin- und Chinazolinderivate mit kombinierter 5-HT1A-, 5-HT1B- und 5-HT1D- Rezeptoraffinität |
| JP2005505506A (ja) | 2001-06-12 | 2005-02-24 | イーラン ファーマスーティカルズ、インコーポレイテッド | アルツハイマー病の治療に有用な大環状分子 |
| DE10149370A1 (de) | 2001-10-06 | 2003-04-10 | Merck Patent Gmbh | Pyrazolderivate |
| AU2003223579A1 (en) | 2002-04-18 | 2003-11-03 | Pharmacia Corporation | Combinations of cox-2 inhibitors and other agents for the treatment of parkinson's disease |
| US20060148858A1 (en) * | 2002-05-24 | 2006-07-06 | Tsuyoshi Maekawa | 1, 2-Azole derivatives with hypoglycemic and hypolipidemic activity |
| AU2003262023A1 (en) | 2002-09-10 | 2004-04-30 | Takeda Pharmaceutical Company Limited | Five-membered heterocyclic compounds |
| WO2004037248A2 (en) * | 2002-10-24 | 2004-05-06 | Carex Sa | Modulation of peroxisome proliferator activated receptors activity |
| DE10315572A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315569A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazolverbindungen |
| DE10315571A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| US20070093492A1 (en) | 2004-03-09 | 2007-04-26 | Weir-Torn Jiaang | Pyrrolidine derivatives |
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2004
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- 2004-03-08 EP EP04718264A patent/EP1611107B1/de not_active Expired - Lifetime
- 2004-03-08 AT AT04718264T patent/ATE478052T1/de active
- 2004-03-08 AU AU2004228121A patent/AU2004228121B2/en not_active Ceased
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- 2004-03-08 CN CNA2004800086295A patent/CN1768043A/zh active Pending
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- 2004-03-08 RU RU2005133990/04A patent/RU2005133990A/ru not_active Application Discontinuation
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- 2004-03-08 BR BRPI0409002-0A patent/BRPI0409002A/pt not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2521202A1 (en) | 2004-10-21 |
| DE10315573A1 (de) | 2004-10-14 |
| MXPA05010646A (es) | 2005-12-12 |
| JP4740116B2 (ja) | 2011-08-03 |
| KR20050119194A (ko) | 2005-12-20 |
| AU2004228121B2 (en) | 2010-11-04 |
| ES2349922T3 (es) | 2011-01-13 |
| AR043838A1 (es) | 2005-08-17 |
| ATE478052T1 (de) | 2010-09-15 |
| AU2004228121A1 (en) | 2004-10-21 |
| JP2006522036A (ja) | 2006-09-28 |
| RU2005133990A (ru) | 2006-03-20 |
| US20070105871A1 (en) | 2007-05-10 |
| ZA200508951B (en) | 2007-03-28 |
| WO2004089910A1 (de) | 2004-10-21 |
| EP1611107A1 (de) | 2006-01-04 |
| US7566709B2 (en) | 2009-07-28 |
| CN1768043A (zh) | 2006-05-03 |
| DE502004011551D1 (de) | 2010-09-30 |
| BRPI0409002A (pt) | 2006-03-28 |
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